Acetonitrile → N-Isopropyl-N-{(3R*,4S*)-4-[(isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzoyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-4-methoxy-3-(3-methoxy-propoxy)-benzamide

HRID 1158487Notes

Reaction equation

HRID 1158487 reaction equation
C([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])[C@@H:10]([CH2:18][N:19]([CH:36]([CH3:38])[CH3:37])[C:20](=[O:35])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[CH2:9]1)C1C=CC=CC=1.[CH3:39][O:40][CH2:41][CH2:42][CH2:43][O:44][C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][C:53]=1[O:54][CH3:55])[C:48](O)=[O:49].CC#N.O.CC#N>O>[CH:36]([N:19]([CH2:18][C@@H:10]1[C@H:11]([CH2:13][N:14]([CH:15]([CH3:17])[CH3:16])[C:48](=[O:49])[C:47]2[CH:51]=[CH:52][C:53]([O:54][CH3:55])=[C:45]([O:44][CH2:43][CH2:42][CH2:41][O:40][CH3:39])[CH:46]=2)[CH2:12][NH:8][CH2:9]1)[C:20](=[O:35])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=1)([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 18373917Acetonitrile--water (1/1)HCID 190395024-Methoxy-3-(3-methoxypropoxy)benzoic acidHCID 59512319N-[(3R*,4R*)-1-Benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

Product 1

HCID 59512502N-Isopropyl-N-{(3R*,4S*)-4-[(isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzoyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-4-methoxy-3-(3-methoxy-propoxy)-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared analogously as described in Example 361 by coupling N-[(3R*,4R*)-1-benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-N-isopropyl4-methoxy-3-(3-methoxy-propoxy)-benzamide and 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid in step J. MS (LC-MS): 658.3 [M+H]+; tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.20 min.

Workup

  1. custom5.20 min.

Sources & evidence

ORD record
ord-33a3f94cb0204297b5bfbb05fa3d4c1f
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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